Category: pyrimidines

Electric Literature of 6960-17-4 ,Some common heterocyclic compound, 6960-17-4, molecular formula is C6H9N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

In 2000ml four bottles in order to join4-Amino-2,5-dimethoxypyrimidine (116.7 g, 0.75 mol)And toluene (188 g),Heated to 70 ~ 75 ,A solution of phenoxycarbonyl isothiocyanate in toluene was added dropwise,About 1 hour drop finished,Continue to heat 2 hours,The reaction was monitored by HPLC.To room temperature,The filter cake was washed twice with 50 ml of ethanol and dried at 60 C to give the desired intermediate4- [4- (2,5-dimethoxypyrimidinyl)] – 3-ThioureaPhenyl ester234.9g, the content is 98.1%, the yield is up to 92.0%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6960-17-4, its application will become more common.

Reference:
Patent; Beijing Yingli Refinement Technology Development Co., Ltd; Hubei Huida Technology Development Co., Ltd; Ling, Yun; Yan, Wei; Huang, Bibo; (7 pag.)CN105294697; (2016); A;,
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Related Products of 114040-06-1, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 114040-06-1, name is 3-Bromo-5,7-dichloropyrazolo[1,5-a]pyrimidine. A new synthetic method of this compound is introduced below.

To a solution of 3-bromo-5,7-dichloropyrazolo[ l ,5-a]pyrimidine (2.67 g, 10 mmol) in DCM (30 mL) at 0 C was added (tetrahydro-2H-pyran-4- yl)methan-amine ( 1 .27 g, 1 1 mmol), followed by DIPEA (2.1 mL, 12 mmol). The resulting mixture was stirred at rt for l h and purified by flash chromatography (gradient: EtOAc hex 0-90%) to give the title compound as white solid (3.46 g, quantitative yield). NMR (400 MHz, CDCl3) delta ppm 7.96 (s, 1 H), 6.55-6.43 (m, 1 H), 6.00 (s, 1H), 4.08-4.00 (m, 2H), 3.43 (dt, J = 12.0, 1.7 Hz, 2H), 3.32 (t, J = 6.6 Hz, 2H), 2.06-1.94 (m, 1H), 1.78-1.71 (m, 2H), 1.51-1.38 (m, 2H); MS ESI [M + H]+345.1, calcd for [C12H14BrClN40+H]+344.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,114040-06-1, 3-Bromo-5,7-dichloropyrazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; LIU, Yong; PAULS, Heinz W.; LAUFER, Radoslaw; LI, Sze-Wan; SAMPSON, Peter Brent; FEHER, Miklos; NG, Grace; PATEL, Narendra Kumar B.; LANG, Yunhui; WO2014/75168; (2014); A1;,
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Electric Literature of 695-87-4, Adding some certain compound to certain chemical reactions, such as: 695-87-4, name is 5-Methoxypyrimidin-4(1H)-one,molecular formula is C5H6N2O2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 695-87-4.

EXAMPLE 4 4-Chloro-5-methoxypyrimidine (VII) Materials: Procedure: To a stirred slurry of 4-hydroxy-5-methoxypyrimidine in toluene (171 mL) was added DIPEA and POCl3 at room temperature under nitrogen atmosphere, The reaction mixture was stirred for about 1-2 hours at 60 to 70 C. under nitrogen atmosphere to complete the reaction. The reaction was quenched by adding 90 mL of 1.55N NaOH at 5 to 8 C. and the aqueous phase was separated. The organic layer was washed with saturated NaHCO3 solution (31 mL) and polish filtered. Concentration of the intermediate was determined by HPLC quantitation. This 0.37 to 0.43M solution of chloromethoxypyrimidine was used without further purification,

According to the analysis of related databases, 695-87-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US5550239; (1996); A;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4472-44-0, 2-Chloro-4,6-dimethylpyrimidine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Computed Properties of C6H7ClN2, blongs to pyrimidines compound. Computed Properties of C6H7ClN2

[0586] Synthesis of methyl 4, 6-dimethylpyrimidine-2-carboxylate: [0587] To a stirred solution of 2-chloro-4, 6-dimethylpyrimidine (1 g, 7.05 mmol) in MeOH: CH3CN (4: 1, 20 mL) under argon atmosphere were added triethyl amine (1.98 mL, 14.02 mmol) and Pd(dppf)2Cl2 (1 g, 1.40 mmol) at room temperature; heated to 100 C and stirred for 20 h under CO pressure in steel bomb. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was filtered through celite and the filtrate was concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 30% EtOAc/ Hexanes to afford methyl 4,6-dimethylpyrimidine-2-carboxylate (400 mg, 34%) as an off- white solid. [0588] 1H-NMR (CDCI3, 400 MHz): delta 7.20 (s, 1H), 4.07 (s, 3H), 2.61 (s, 6H); LC-MS: 87.29%; 167.2 (M++l); (column: X-Bridge C-18, 50 3.0 mm, 3.5 mupiiota); RT 1.47 min. 0.05% Aq TFA: ACN; 0.8 mL/min); TLC: 30% EtOAc/ Hexanes (R 0.3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4472-44-0, 2-Chloro-4,6-dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
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Electric Literature of 101257-82-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 101257-82-3, name is 4-Amino-5-chloropyrimidine, molecular formula is C4H4ClN3, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

L. [4-(3-Chloropropylsulfanyl)-3-methylpyridin-2-ylmethyl]-(5-chloropyrimidin-4-yl)amine A solution of 2.7 g (20.85 mmol) of 4-amino-5-chloropyrimidine in 20 ml of dimethylformamide is added dropwise to a suspension of 0.75 g (18.25 mmol) of sodium hydride (60% strength in paraffin) in 5 ml of dimethylformamide. The mixture is stirred at room temperature for 20 minutes. A solution of 5 g (17.38 mmol) of 2-chloromethyl-4-(3-chloropropylsulfanyl)-3-methylpyridine in 5 ml of dimethylformamide is then added dropwise in the course of 30 minutes and the mixture is then stirred at room temperature for 4 hours. It is concentrated in a high vacuum and the residue is taken up in 150 ml of water and 100 ml of dichloromethane with vigorous stirring. The aqueous phase is extracted with 3*50 ml of dichloromethane. The organic extracts are dried over magnesium sulfate and concentrated. The residue is purified by chromatography on silica gel (eluent: toluene/ethyl acetate/methanol/conc. ammonia=6/3.5/0.5/0.05). The elude is concentrated and the residue is then digested with diethyl ether. After filtration and drying of the precipitate, 2.8 g (47%) of the title compound are obtained as a colorless solid, which is used without further purification.

According to the analysis of related databases, 101257-82-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BYK Gulden Lomberg Chemische Fabrik GmbH; US6395732; (2002); B1;,
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Adding a certain compound to certain chemical reactions, such as: 815610-16-3, 2-Amino-4-iodopyrimidine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 815610-16-3, blongs to pyrimidines compound. Recommanded Product: 815610-16-3

A flask containing a solution of 55-iodide (4.09g, 18.5mmol) in NMP (75ml) was purged with argon for 5min. Zinc cyanide (2.28g, 19.4mmol) and tetrakis(triphenylphosphine)palladium (0) (1.71g, 1.48mmol) were added and the mixture was stirred at 80C for 2h. The mixture was cooled to room temperature, EtOAc (200ml) and 30% aqueous NH4OH (200ml) was added, and stirring was continued for 1h. The layers were separated, the aqueous layer was extracted with EtOAc (4×200ml), and the combined organic layers were concentrated under reduced pressure. Et2O (30ml) was added and the precipitate was collected by filtration and washed with Et2O to deliver 2-aminopyrimidine-4-carbonitrile (1.66g, 13.8mmol, 75% yield) as a white solid. 1H NMR (400MHz, DMSO-d6) delta ppm 8.51 (d, J=4.7Hz, 1H), 7.31 (br. s, 2H), 7.08 (d, J=4.7Hz, 1H). MS (ESI, pos. ion) m/z: 121.1 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,815610-16-3, its application will become more common.

Reference:
Article; Reichelt, Andreas; Bailis, Julie M.; Bartberger, Michael D.; Yao, Guomin; Shu, Hong; Kaller, Matthew R.; Allen, John G.; Weidner, Margaret F.; Keegan, Kathleen S.; Dao, Jennifer H.; European Journal of Medicinal Chemistry; vol. 80; (2014); p. 364 – 382;,
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Synthetic Route of 51953-18-5, Adding some certain compound to certain chemical reactions, such as: 51953-18-5, name is Pyrimidin-4-ol,molecular formula is C4H4N2O, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 51953-18-5.

(b) 4, [5-DICHLOROPYRIMIDINE.] A solution of the pyrimidin-4-one from step (a) above (3.5 g, 26.8 mmol) in phosphorus oxychloride (50 mL) was heated under for 3 h. The reaction mixture was cooled to room temperature, the solvent was evaporated [IN VACUO] and the residue was dissolved in EtOAc (100 mL). The organic solution was washed with saturated aqueous solution of NaHC03 (50 mL) and brine [(50] mL), dried over [NA2S04,] filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography, eluting with 10% [ETOAC/HEXANE,] to give the title compound as an orange oil. MS (ESI, pos. [ION) M/Z] : 131 [(M+1).]

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 51953-18-5, Pyrimidin-4-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; WO2004/35549; (2004); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 60025-06-1, 1-(4,6-Dichloropyrimidin-5-yl)ethanone, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

Synthesis of Compound 6.1. Hydrazine hydrate (107 uL, 2.20 mmol) was slowly added to a solution of 1-(4,6-dichloro-pyrimidin-5-yl)-ethanone (Clark, J. et al J. Chem. Soc. 1976, 9, 1004) (400 mg, 2.09 mmol) and triethylamine (280 uL, 2.0 mmol) in 1,4-dioxane (7 mL) at 8 C. After the addition was complete, the reaction mixture was warmed to RT. After 2.5 hr, the reaction mixture was filtered through celite and then evaporated to afford compound 6.1 (200 mg) as a yellow solid. 1H-NMR (400.13 MHz, DMSO-d6) 14.07 (s, 1H), 8.75 (s, 1H), 2.64 (s, 3H). MS m/z 169 [M+1]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60025-06-1, 1-(4,6-Dichloropyrimidin-5-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; Sunesis Pharmaceuticals, Inc; US2009/5359; (2009); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 108-53-2, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.108-53-2, name is 2-Aminopyrimidin-4(1H)-one, molecular formula is C4H5N3O, molecular weight is 111.102, as common compound, the synthetic route is as follows.

In a three neck IL round bottom flask equipped with reflux condenser was added 2-amino- 4(3H)-pyrimidinone A.ll (10Og, 0.9 mol) (available from Toronto Research Chemicals) followed by POCl3 (168 ml, 1.800mol) at room temperature and under an atmosphere of N2. To this was cautiously added ClSO3H (4.8ml, 72.01 mmol). The solution was heated to 950C for 4 hrs, before it was cooled to room temperature. The solution was then cooled in an ice bath before it was poured into 700ml of ice water with vigorous stirring. Adjusted the pH to ~7 with NH4OH (30% by weight) (temperature was held below 2O0C). A tan colored solid was collected by filtration. The solid was dried under vacuum at 7O0C overnight to afford 4-chloro- 2-pyrimidinamine A.12 (108g, 92%) as an off white solid.1H NMR (400 MHz, (CD)3SO) delta 8.17 (d, J = 5.2 Hz, IH), 7.07 (br s, 2H), 6.64 (d, J = 5.2 Hz, IH); ESI MS: M + H+ 130.0 m/z.

Statistics shows that 108-53-2 is playing an increasingly important role. we look forward to future research findings about 2-Aminopyrimidin-4(1H)-one.

Reference:
Patent; AMGEN INC.; WO2009/158011; (2009); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 1801-06-5, name is 4-Chloro-5-fluoro-2-methoxypyrimidine. A new synthetic method of this compound is introduced below., Product Details of 1801-06-5

General conditions1: Chloropyrimidine 5 (0.45 mmol) and aminopyrazole 6 (0.30 mmol) were mixed in 1:1 acetic acid/water solution (1.4 mL) or in glacial acetic acid (1.4 mL) and stirred at 100 °C in an oil bath for 1 h (or 50 °C for 4 h or 25 °C for 18 h). The mixture was neutralized by the addition of ice-cold 5percent NaOH solution (10 mL) and extracted with methylene chloride (3 .x. 25 mL). Combined organic layers were dried and concentrated. The residue was further purified by normal phase flash chromatography (Biotage, for cPropylphenyl analogs R = C) or reversed phase preparative HPLC (analogs with free amines R = A or B), affording the desired aminopyrimidines (7-30).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 1801-06-5, 4-Chloro-5-fluoro-2-methoxypyrimidine.

Reference:
Article; Guo, Chuangxing; Dong, Liming; Marakovits, Joseph; Kephart, Susan; Tetrahedron Letters; vol. 52; 14; (2011); p. 1692 – 1696;,
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